ES2330107T3 - Derivados de urea heterociclicos para el tratamiento del dolor. - Google Patents

Derivados de urea heterociclicos para el tratamiento del dolor. Download PDF

Info

Publication number: ES2330107T3
Authority: ES; Spain
Prior art keywords: compounds; compound; formula; pain; baselineskip
Prior art date: 2003-03-06
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Lifetime

Application number

ES04717691T

Other languages

English (en)

Spanish (es)

Inventor

Stephen Frederick Moss

Harshad Kantilal Rami

Mervyn Thompson

David Richard Witty

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Glaxo Group Ltd

Original Assignee

Glaxo Group Ltd

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2003-03-06

Filing date

2004-03-05

Publication date

2009-12-04

2003-03-06 Priority claimed from GB0305165A external-priority patent/GB0305165D0/en

2003-07-15 Priority claimed from GB0316554A external-priority patent/GB0316554D0/en

2004-03-05 Application filed by Glaxo Group Ltd filed Critical Glaxo Group Ltd

2009-12-04 Application granted granted Critical

2009-12-04 Publication of ES2330107T3 publication Critical patent/ES2330107T3/es

2024-03-05 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

238000011282 treatment Methods 0.000 title claims description 13
208000002193 Pain Diseases 0.000 title claims description 12
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 title description 7
239000004202 carbamide Substances 0.000 title description 4
150000001875 compounds Chemical class 0.000 claims abstract description 87
150000003839 salts Chemical class 0.000 claims abstract description 25
239000012453 solvate Substances 0.000 claims abstract description 20
229910052698 phosphorus Inorganic materials 0.000 claims abstract description 7
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 5
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 14
208000035475 disorder Diseases 0.000 claims description 11
238000011321 prophylaxis Methods 0.000 claims description 5
239000003814 drug Substances 0.000 claims description 4
239000000546 pharmaceutical excipient Substances 0.000 claims description 3
230000008485 antagonism Effects 0.000 claims description 2
230000009286 beneficial effect Effects 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
239000000126 substance Substances 0.000 claims description 2
229940079593 drug Drugs 0.000 claims 1
230000001225 therapeutic effect Effects 0.000 claims 1
238000000034 method Methods 0.000 abstract description 37
238000002560 therapeutic procedure Methods 0.000 abstract description 4
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 34
239000000243 solution Substances 0.000 description 21
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
238000006243 chemical reaction Methods 0.000 description 14
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
YKPUWZUDDOIDPM-SOFGYWHQSA-N capsaicin Chemical compound COC1=CC(CNC(=O)CCCC\C=C\C(C)C)=CC=C1O YKPUWZUDDOIDPM-SOFGYWHQSA-N 0.000 description 12
102000011040 TRPV Cation Channels Human genes 0.000 description 11
108010062740 TRPV Cation Channels Proteins 0.000 description 11
239000000203 mixture Substances 0.000 description 11
238000002360 preparation method Methods 0.000 description 11
239000007787 solid Substances 0.000 description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
239000002253 acid Substances 0.000 description 10
-1 Heterocyclic urea derivatives Chemical class 0.000 description 9
239000003981 vehicle Substances 0.000 description 9
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
239000003921 oil Substances 0.000 description 8
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
239000000047 product Substances 0.000 description 6
239000000725 suspension Substances 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
235000017663 capsaicin Nutrition 0.000 description 5
229960002504 capsaicin Drugs 0.000 description 5
230000000694 effects Effects 0.000 description 5
238000001819 mass spectrum Methods 0.000 description 5
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OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 4
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JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
229910052786 argon Inorganic materials 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
239000011575 calcium Substances 0.000 description 4
229910052791 calcium Inorganic materials 0.000 description 4
239000000284 extract Substances 0.000 description 4
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QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
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150000001412 amines Chemical class 0.000 description 3
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DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 3
150000003672 ureas Chemical class 0.000 description 3
ZWHDLUCBDCSQQN-SSDOTTSWSA-N (3r)-1-(3-chloropyridin-2-yl)pyrrolidin-3-amine Chemical compound C1[C@H](N)CCN1C1=NC=CC=C1Cl ZWHDLUCBDCSQQN-SSDOTTSWSA-N 0.000 description 2
NSPFGXPPFDWZEM-SSDOTTSWSA-N (3r)-1-[3-(trifluoromethyl)pyridin-2-yl]pyrrolidin-3-amine Chemical compound C1[C@H](N)CCN1C1=NC=CC=C1C(F)(F)F NSPFGXPPFDWZEM-SSDOTTSWSA-N 0.000 description 2
ZGMOVZMXQTVQSO-UHFFFAOYSA-N 1,3-dimethyl-5-nitroisoquinoline Chemical compound C1=CC=C2C(C)=NC(C)=CC2=C1[N+]([O-])=O ZGMOVZMXQTVQSO-UHFFFAOYSA-N 0.000 description 2
SNQSGKQEGKHJCZ-UHFFFAOYSA-N 1,3-dimethylisoquinoline Chemical compound C1=CC=C2C(C)=NC(C)=CC2=C1 SNQSGKQEGKHJCZ-UHFFFAOYSA-N 0.000 description 2
JLSHUNFRPIXXPK-UHFFFAOYSA-N 1-(3,4-difluorophenyl)piperidin-4-amine Chemical compound C1CC(N)CCN1C1=CC=C(F)C(F)=C1 JLSHUNFRPIXXPK-UHFFFAOYSA-N 0.000 description 2
LUHIHXNLKDWPIF-UHFFFAOYSA-N 1-(3-chloro-6-methoxypyridin-2-yl)piperidin-4-amine Chemical compound COC1=CC=C(Cl)C(N2CCC(N)CC2)=N1 LUHIHXNLKDWPIF-UHFFFAOYSA-N 0.000 description 2
JXJWLMJMQMBXMI-UHFFFAOYSA-N 1-(6-methoxypyridin-2-yl)piperidin-4-amine Chemical compound COC1=CC=CC(N2CCC(N)CC2)=N1 JXJWLMJMQMBXMI-UHFFFAOYSA-N 0.000 description 2
TUQLCRAOVWMKSX-UHFFFAOYSA-N 1-[3-bromo-5-(trifluoromethyl)pyridin-2-yl]piperidin-4-amine Chemical compound C1CC(N)CCN1C1=NC=C(C(F)(F)F)C=C1Br TUQLCRAOVWMKSX-UHFFFAOYSA-N 0.000 description 2
KTVCRQQSDOZEPA-UHFFFAOYSA-N 1-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]piperidin-4-amine Chemical compound C1CC(N)CCN1C1=NC=C(C(F)(F)F)C=C1Cl KTVCRQQSDOZEPA-UHFFFAOYSA-N 0.000 description 2
CNBQWWYEPQQHDA-UHFFFAOYSA-N 1-[3-chloro-6-(trifluoromethyl)pyridin-2-yl]piperidin-4-amine Chemical compound C1CC(N)CCN1C1=NC(C(F)(F)F)=CC=C1Cl CNBQWWYEPQQHDA-UHFFFAOYSA-N 0.000 description 2
DQNINWHWNWCYFQ-UHFFFAOYSA-N 1-[3-methyl-5-(trifluoromethyl)pyridin-2-yl]piperidin-4-amine Chemical compound CC1=CC(C(F)(F)F)=CN=C1N1CCC(N)CC1 DQNINWHWNWCYFQ-UHFFFAOYSA-N 0.000 description 2
FBAOOCXFUXICRT-UHFFFAOYSA-N 1-[4-(trifluoromethyl)pyrimidin-2-yl]piperidin-4-amine Chemical compound C1CC(N)CCN1C1=NC=CC(C(F)(F)F)=N1 FBAOOCXFUXICRT-UHFFFAOYSA-N 0.000 description 2
HWIOQDVSPMQAGI-UHFFFAOYSA-N 1-[6-(trifluoromethyl)pyridin-2-yl]piperidin-4-amine Chemical compound C1CC(N)CCN1C1=CC=CC(C(F)(F)F)=N1 HWIOQDVSPMQAGI-UHFFFAOYSA-N 0.000 description 2
KCFPJVLNUUNVGL-UHFFFAOYSA-N 1-[6-methoxy-3-(trifluoromethyl)pyridin-2-yl]piperidin-4-amine Chemical compound COC1=CC=C(C(F)(F)F)C(N2CCC(N)CC2)=N1 KCFPJVLNUUNVGL-UHFFFAOYSA-N 0.000 description 2
GECJKFNXMPCRQE-UHFFFAOYSA-N 1-[6-methoxy-5-(trifluoromethyl)pyridin-2-yl]piperidin-4-amine Chemical compound C1=C(C(F)(F)F)C(OC)=NC(N2CCC(N)CC2)=C1 GECJKFNXMPCRQE-UHFFFAOYSA-N 0.000 description 2
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KBDMNBWTHOKXQA-UHFFFAOYSA-N 1-methylisoquinolin-5-amine Chemical compound C1=CC=C2C(C)=NC=CC2=C1N KBDMNBWTHOKXQA-UHFFFAOYSA-N 0.000 description 2
RXATZPCCMYMPME-UHFFFAOYSA-N 2-chloro-3-(trifluoromethyl)pyridine Chemical compound FC(F)(F)C1=CC=CN=C1Cl RXATZPCCMYMPME-UHFFFAOYSA-N 0.000 description 2
ADVQMCQMDHBTHJ-UHFFFAOYSA-N 2-chloro-6-(trifluoromethyl)pyridine Chemical compound FC(F)(F)C1=CC=CC(Cl)=N1 ADVQMCQMDHBTHJ-UHFFFAOYSA-N 0.000 description 2
DYAGVPKVELUYPJ-UHFFFAOYSA-N 3-(trifluoromethyl)pyridin-4-amine Chemical compound NC1=CC=NC=C1C(F)(F)F DYAGVPKVELUYPJ-UHFFFAOYSA-N 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
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FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
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238000012360 testing method Methods 0.000 description 2
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- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
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Landscapes

Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Pain & Pain Management (AREA)
Biomedical Technology (AREA)
Pulmonology (AREA)
Neurosurgery (AREA)
Diabetes (AREA)
Neurology (AREA)
Endocrinology (AREA)
Cardiology (AREA)
Urology & Nephrology (AREA)
Heart & Thoracic Surgery (AREA)
Rheumatology (AREA)
Orthopedic Medicine & Surgery (AREA)
Vascular Medicine (AREA)
Emergency Medicine (AREA)
Immunology (AREA)
Hematology (AREA)
Physical Education & Sports Medicine (AREA)
Reproductive Health (AREA)
Obesity (AREA)
Dermatology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Pyridine Compounds (AREA)

ES04717691T 2003-03-06 2004-03-05 Derivados de urea heterociclicos para el tratamiento del dolor. Expired - Lifetime ES2330107T3 (es)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
GB0305165		2003-03-06
GB0305165A GB0305165D0 (en)	2003-03-06	2003-03-06	Novel compounds
GB0316554		2003-07-15
GB0316554A GB0316554D0 (en)	2003-07-15	2003-07-15	Novel compounds

Publications (1)

Publication Number	Publication Date
ES2330107T3 true ES2330107T3 (es)	2009-12-04

Family

ID=32964071

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
ES04717691T Expired - Lifetime ES2330107T3 (es)	2003-03-06	2004-03-05	Derivados de urea heterociclicos para el tratamiento del dolor.

Country Status (7)

Country	Link
US (1)	US7528151B2 (de)
EP (1)	EP1603899B1 (de)
JP (1)	JP2006519826A (de)
AT (1)	ATE440835T1 (de)
DE (1)	DE602004022783D1 (de)
ES (1)	ES2330107T3 (de)
WO (1)	WO2004078749A1 (de)

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Publication number	Priority date	Publication date	Assignee	Title
US7514562B2 (en)	2003-03-07	2009-04-07	Glaxo Group Limited	Urea derivatives and their use as vanilloid receptor antagonists in the treatment of pain
GB0305426D0 (en)	2003-03-08	2003-04-16	Glaxo Group Ltd	Novel compounds
DE102005062991A1 (de) *	2005-12-28	2007-07-05	Grünenthal GmbH	Substituierte Thiazole und ihre Verwendung zur Herstellung von Arzneimitteln
DE102005062990A1 (de) *	2005-12-28	2007-07-05	Grünenthal GmbH	Substituierte Thiazole und ihre Verwendung zur Herstellung von Arzneimitteln
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WO2009034433A2 (en) *	2007-09-10	2009-03-19	Glenmark Pharmaceuticals, S.A.	3-azabicyclo [3.1.0] hexane derivatives as vanilloid receptor ligands
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- 2004-03-05 JP JP2006505928A patent/JP2006519826A/ja active Pending
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Publication number	Publication date
JP2006519826A (ja)	2006-08-31
US7528151B2 (en)	2009-05-05
ATE440835T1 (de)	2009-09-15
US20070117820A1 (en)	2007-05-24
DE602004022783D1 (de)	2009-10-08
WO2004078749A1 (en)	2004-09-16
EP1603899B1 (de)	2009-08-26
EP1603899A1 (de)	2005-12-14

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